New acid dyestuffs of the anthraquinone series



' l d R for hydrogen, or R and R repchloride to react with dimethylamine and Patented Aug. 30, 1932 1,875,1M

UNITED STATES PATENT OFFICE HEINRICH KOGILlOF FBANKFORT-ON-THE-MAIN, GERMANY, ASSIGNOR T0 GENERAL ANILINE wonxs, mo, OF NEW YORK, N. Y., A CORPORATION OF DELAWARE NEW ACID DYESTUFFS OF THE AN THRAQUINONE SERIES v No Drawing. Applica'tionfiled January 5, 1932, Serial No. 584,895, and in Germany March 20, 1930.

The present invention relates to new acid stuffs is by condensing a QA-dihalogen-ldyestuffs of the anthraquinone series, more aminoanthraquinone with a 2-amino-5.6.7.8- particularly it relates to new compounds of. tetrahydronaphthalene-sulfontmide comthe general formula: pound as identified in the last general for- 0 NH," 1 mula and exchanging the halogen atom in H SOaH the 2-position of the anthraquinone nucleus for the sulfonic acid. group according to known methods, for instance, by treatment with an alkali metal sulfite. w The following examples serve to illustrate the invention, but they are not intended to limit it thereto, the parts being by weight;

(1) A mixture of 40 parts of l-amino-lbromoanthraquinone-Q-sodium sulfonate, 36 parts of 2-amino-5.6.7;8-tetrahydronaphtha lene l-sulfonic acid-dimethyla'mide, melting wherein R stands for a radical of the group at 1390 (Obtamable y causmg 1 consisting of alkyl, hydroxyalkyl and cyclo- 5.6.7.S-tetrahydronaphthalene-4-sulfon1c ac1d resent lk l radicalg subsequent reduction of the nitro-group), My new dyestuffs yield on wool from an 200 parts of water, 100 parts of alcohol, 12 acid bath clear blue tints of good fastness parts of sodiumbicarbonate and 1 part of properties, particularly as to Washing, fulling cuprous chloride is gently boiled for several and to sea-water. They are obtainable by h causing 13min04"ha10gena-nthl'aquinonejg' The blue dyestufl thus obtained corresulfonic acid or a salt thereof to react with d 'r h following f l a compound of the general formula: D 0 N BOaH d EN 7 El 35 0H2 MY (1H2 wherein R and R are identified as above. 2

The condensation of the compounds is prefo2 erably effected by heating them in the pres- 0 ence of water, an acid binding agent, such'as sodium carbonate or sodiumbicarbon'at'e, and p asmall quantity of a'catalitically acting sub- T y P P from the stance, such as cuprous chloride, coppersulaction mixture by addltlon of commonsalt.

fateor the like. '1 It may be purified by IG-dlSSOlVlIlglt in Another way of preparing the'new dyewater and again precipitating it by means no v e g 1,875,191

ofcommon salt. The isolated and dried dyesulfofhic acid-cyclohexylamide, a blue dye- Stuff forms a blue p d r; it ye W001 {r0111 stuff of good fastness properties is obtained. an acid bath clear blue tints of g vfastness It corresponds with the following formula I to washing, to fulling and to sea-water. V 1 I 4O parts'of l-aminol-bromoanthmquinone-Q-sodium sulfonate and 35 parts'of 2-a1nino-5.6.7.8-tetrahydronaphthalene 1 sulfonie ,acid-methylamide (melting point 166 C.) are heated to boiling for several hours in 160 parts of water and 80 parts of alcohol in the presence of 12 parts of sodiumbicarbonate, 4 parts of sodium carbonate and l part of cuprou's'chloride. v V i I 'qThe dyestl fl' hus vformed is separated 15 .from' the reaction mixture. may be pu-f", f

-' rifled by re-dissolving it in water and again H -reprecipitatingit by means of common salt; i It'dyes wool from an acid bath'bliietintsof V V good vfastness to washing and'to vfulling; .16. ;PQQQJQZ XQK PE ffim l 9 e 20' The dyestufl has the f ll i f r l 2a1n1no-5.6.7 .8-tetrahydronaphthalene 4: 9185 W 1 Y siilfoniclacideclimethylamide, 4 1 partsjofllZ-l amino-4-5.6.7.8'- tetrahydronaphthalene {1 isulfonic acid-diethylamide 5 (melting 1 point 7 132 C.-to 133 (3.), 'a, 'bl-ue dyestiifi' is ob tained dyeing wool froin an acid bath blue tints of good'fastness properties. -The dyestufi' has the following formula: 2

' O NE? I v 'mo H i 5 10 parts of i 1-a1nino-4 -vbrornoanthra'- =genome-sodium81111011318 are heated to 0..t0'90? C. for several hoiirs with 36 parts oi. v 2-amino-5.6.7.8 tetrahydronaphthalenelf 1 'sulfonic acid ethanol ainide '(melting point i 108 C. to 109 C.) in 200 parts of'water and I in the presence of 16, parts of sodiulnbica'rbonat'e, 4 parts of sodium carbonate and 0.5 part of cuprous chloride! 7 i v '11.: Agnew products; the compounds of the The dyestuff 1s punfiedas stated 111 EX% l'fofl I By usingin Exem'ple l instead of 86 heXyl and, R5101 {'hy'drogen,-orBifand gltg 7 parts of 2- amino-5.6.7.8 tetrzphydronaphthae represent alkylradicals ssid products-yield l lene-4-sulfonic aeid-d'ZInethylamid-e, 4 1-pa'rts ing onwool froma'n acid btthelejar bliie' tints I 65 of":2 a1nino 5.6:7.8 tetrahyd-ronaphthalenwl of good fastnesspropel' ie i 180 anr1ple 1. g It dyes Wool from an acid'beth v 70 clearblnetints of good fastness properties. 5 v

7 The dyestuff has the-following formula: 1 1'- p r o 'nm V w o I v 5.0 j r 7:11.75

' V ,7 c0 7 ,7 V P I V s wherein R stands for a radlc a lof the group 2. As a new product, the compound of the formula (I? N Ha a i v HN EH: JH Hz 802 I LEAH,

being in the dry state a blue powder, dyeing wool from an acid bath clear blue tints of good fastness to washing, to fulling and to seawater.

3. As a new product, the compound of the formula O NH: I I 808E H: HN A d \H:

III HaG \H being in the dry state a blue powder, dyeing Wool from an acid bath blue tints of good fastness to washing and to fulling.

4. As a new product, the compound of the formula:

O NH:

I Y I 80:11

1:2 7 EN x11:

r N H0346: \H

being in the dry state a blue powder, dyeing wool from an acid bath blue tints of good fastness properties. I so In testimony whereof, I aflix my signature.

' HEINRICH KOCH. 

